1,4,7,10,14,17,20,23,27,30,33,36-dodecaoxacyclononatriacontane-11,13,24,26,37,39-hexaone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4,7,10,14,17,20,23,27,30,33,36-dodecaoxacyclononatriacontane-11,13,24,26,37,39-hexaone
• 英文别名: 1,4,7,10,14,17,20,23,27,30,33,36-Dodecaoxacyclononatriacontane-11,13,24,26,37,39-hexone
• 化学式: C₂₇H₄₂O₁₈
• 分子量: 654.62
• InChiKey: NSZVTLIARKRBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  45
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1,4,7,10,14,17,20,23,27,30,33,36-dodecaoxacyclononatriacontane-11,13,24,26,37,39-hexaone 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到12,25,38-trisdiazo-1,4,7,10,14,17,20,23,27,30,33,36-dodecaoxacyclononatriacontane-11,13,24,26,37,39-hexaone
  参考文献：
  名称：

  Reactions of macrocyclic rhodium carbenoids: regioselective synthesis of indol-3-yl macrocyclic lactones and cryptands

  摘要：

  A wide variety of new macrocyclic diazocarbonyl compounds with various spacers was synthesized. Macrocyclic rhodium(H) carberioid insertion with various substituted indoles was performed to afford regioselectively, indol-3-yl macrocyclic di- or tetralactones (C3-alkylation). Double carberioid insertion was also performed to afford indolyl cryptand molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.102
• 作为产物：
  描述：

  丙二酰氯 、 三乙二醇 在 potassium fluoride 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 以16.2%的产率得到1,4,7,10,14,17,20,23-octaoxacyclohexacosane-11,13,24,26-tetraone
  参考文献：
  名称：

  Selective Syntheses of Novel Polyether Fullerene Multiple Adducts

  摘要：

  We have applied a modified macrocyclic tether approach to control multiple additions to C-60. The technique of He-3 NMR was used to confirm the selective formation of specific C-60 multiple adducts by the macrocyclic tether approach. An oligoglycol was used as a flexible linker to produce macrocyclic polyether-linked malonates 5, 6, 8, and 9 under solid-liquid PTC (phase-transfer-catalysis) conditions. The formation of a single C60 tris-adduct, 3, from macrocyclic malonate 1 and (HeC60)-He-3-C-@ was proven by He-3 NMR. Similarly, multiple additions to C-60 of macrocyclic polyether malonate 5 gave C-60 bis-adduct 10 selectively, while the reaction of C-60 with macrocyclic malonate 8 gave bis-adducts 11 and 12. A similar process with macrocyclic malonate 6 gave tris-adduct 13 with high selectivity as well. Saponification of these C-60 multiple adducts gives the corresponding polyacids that are potentially useful in biological applications. Macrocyclic polyether fullerenes are a new class of ionophores, which could be interesting for molecular recognition and for the development of biosensors.

  DOI：

  10.1021/jo034542l

文献信息

• Selective Syntheses of Novel Polyether Fullerene Multiple Adducts
  作者：Zhiguo Zhou、David I. Schuster、Stephen R. Wilson

  DOI：10.1021/jo034542l

  日期：2003.10.1

  We have applied a modified macrocyclic tether approach to control multiple additions to C-60. The technique of He-3 NMR was used to confirm the selective formation of specific C-60 multiple adducts by the macrocyclic tether approach. An oligoglycol was used as a flexible linker to produce macrocyclic polyether-linked malonates 5, 6, 8, and 9 under solid-liquid PTC (phase-transfer-catalysis) conditions. The formation of a single C60 tris-adduct, 3, from macrocyclic malonate 1 and (HeC60)-He-3-C-@ was proven by He-3 NMR. Similarly, multiple additions to C-60 of macrocyclic polyether malonate 5 gave C-60 bis-adduct 10 selectively, while the reaction of C-60 with macrocyclic malonate 8 gave bis-adducts 11 and 12. A similar process with macrocyclic malonate 6 gave tris-adduct 13 with high selectivity as well. Saponification of these C-60 multiple adducts gives the corresponding polyacids that are potentially useful in biological applications. Macrocyclic polyether fullerenes are a new class of ionophores, which could be interesting for molecular recognition and for the development of biosensors.
• Reactions of macrocyclic rhodium carbenoids: regioselective synthesis of indol-3-yl macrocyclic lactones and cryptands
  作者：Sengodagounder Muthusamy、Boopathy Gnanaprakasam

  DOI：10.1016/j.tetlet.2007.11.102

  日期：2008.1

  A wide variety of new macrocyclic diazocarbonyl compounds with various spacers was synthesized. Macrocyclic rhodium(H) carberioid insertion with various substituted indoles was performed to afford regioselectively, indol-3-yl macrocyclic di- or tetralactones (C3-alkylation). Double carberioid insertion was also performed to afford indolyl cryptand molecules. (C) 2007 Elsevier Ltd. All rights reserved.